L-Malic Acid → HCID 131722769, compound

HRID 1636056Notes

Reaction equation

HRID 1636056 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH2:50][N:51]2[CH:55]=[N:54][CH:53]=[N:52]2)[O:13][CH:12]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:27][CH2:26][N:25]([C:28]4[CH:33]=[CH:32][C:31]([N:34]5[C:38](=[O:39])[N:37]([CH:40]([C:47]([OH:49])=[O:48])[CH2:41][NH:42][CH:43]([CH3:46])[CH2:44][CH3:45])[N:36]=[CH:35]5)=[CH:30][CH:29]=4)[CH2:24][CH2:23]3)=[CH:18][CH:17]=2)[CH2:11][O:10]1.[OH:56][C@@H:57]([CH2:61][C:62]([OH:64])=[O:63])[C:58]([OH:60])=[O:59]>C(O)C>[OH:56][C@@H:57]([CH2:61][C:62]([OH:64])=[O:63])[C:58]([OH:60])=[O:59].[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH2:50][N:51]2[CH:55]=[N:54][CH:53]=[N:52]2)[O:13][CH:12]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:27][CH2:26][N:25]([C:28]4[CH:29]=[CH:30][C:31]([N:34]5[C:38](=[O:39])[N:37]([CH:40]([C:47]([OH:49])=[O:48])[CH2:41][NH:42][CH:43]([CH3:46])[CH2:44][CH3:45])[N:36]=[CH:35]5)=[CH:32][CH:33]=4)[CH2:24][CH2:23]3)=[CH:18][CH:17]=2)[CH2:11][O:10]1

Participants

4

Reactant 2

HCID 222656L-Malic AcidHCID 131722770HCID 131722770, compound

Product 1

HCID 131722769HCID 131722769, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

[2S-[2α,4α[(R*,R*)]]]-2-[4-[4-[4-[4-[[2-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-4,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl]-1-methylpropyl β-alanine (0.0028 mol) was dissolved in warm ethanol (25 ml). (−)-(S)-hydroxybutanedioic acid (0.0061 mol) was added and the mixture was parboiled until complete dissolution. The resulting clear solution was allowed to cool to room temperature and the solvent was evaporated. The residue was stirred in 2-propanone, filtered off, then dried, yielding 1.53 g (53%) [2S-[2α,4α-[(R*,R*)]]]-2-[4-[4-[4-[4-[[2-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-4,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl]-1-methylpropyl β-alanine (S)-hydroxybutanedioate(1:2) monohydrate (compound 12).

Workup

  1. dissolutionthe mixture was parboiled until complete dissolution
  2. customthe solvent was evaporated
  3. filtrationfiltered off
  4. customdried

Sources & evidence

ORD record
ord-28b1b24888ab4ba4b9805f91c7883df0
Source dataset
uspto-grants-2003_01
Patent number
US06512116B2

Reaction notes

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